Across

Esquire (Singapore) - - Cover Story -

two coasts and three days, Bern­thal told me tales of his boy­hood that in­cluded more than a few mo­ments of dys­func­tion and rage. He blithely con­fessed to things other peo­ple would keep hid­den, and he seemed to do it not out of a sense of machismo but with a sense of won­der that the world had given him such a long leash. Lis­ten­ing to his sto­ries about hang­ing around the up­per-class out­casts of DC, I kept think­ing of Glen, the sage and pos­si­bly dis­turbed friend of Sally Draper on Mad Men.

As a boy, Bern­thal drew pic­tures of a guinea pig and a dog shoot­ing teens with a cross­bow. He got sent home early from a camp­ing trip at age eight for traf­fick­ing copies of Play­boy. And he had a vi­o­lent side. At school, he watched his brother Tom meekly roll the ball back to an ad­ver­sary dur­ing dodge­ball. When the boy mocked Tom, Bern­thal picked up an­other ball and whipped it into a stack of chairs near his brother’s tor­men­tor. The force of the throw knocked the chairs on top of the kid.

But Bern­thal also wants you to know that he came from a pros­per­ous, car­ing fam­ily. His fa­ther was a pow­er­ful cor­po­rate lawyer in DC, and his mother watched over a hand­ful of fos­ter kids in ad­di­tion to her three boys. The fam­ily lived in a tony sub­ur­ban neigh­bor­hood, and Bern­thal at­tended Sid­well Friends, where Chelsea Clin­ton was a few grades be­low him.

Bern­thal was the mid­dle brother, and he quickly es­tab­lished him­self as the fam­ily en­forcer. By un­spo­ken agree­ment, he was the one to take re­venge when­ever his fa­ther or broth­ers got cheap-shot­ted in the reg­u­lar bas­ket­ball game they played when he was a kid. “They knew I would pro­tect them,” Bern­thal told me.

At Sid­well, he says, “we were sub­ur­ban kids, but we all wanted to find the most dan­ger­ous things in a dan­ger­ous city.” The fact that they went to a posh school gave them a larger chip on their blaz­ers. They fought kids from other schools with nun­chakus and fists, and spent a lot of af­ter­noons run­ning from the cops.

When he was 17, Bern­thal got caught by a DC po­lice­man with some dime bags. He was taken to jail and put in a cell. “One thing that I’ve al­ways been afraid of, my whole life, was crick­ets,” Bern­thal told me at an Ojai biker bar. “I get into this jail cell and I’m sit­ting there and I see there’s two crick­ets in there.” An older man was put in the cell with Bern­thal, which scared him un­til the man crushed the crick­ets. “I told him I was wor­ried about how my dad was go­ing to re­act to me get­ting ar­rested. He said he’d been in and out for 20 years and never heard some­one men­tion their dad.”

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